The Creative Class | Nickelson Wooster, Creative Director

Nick Wooster Photo: Tommy Ton

Nick Wooster | Photo: Tommy Ton

NEW YORK, United States — He has been ordained “the alpha male of American street style” by GQ and called “Woost God” by some of his most rabid fans. But Nickelson 'Nick' Wooster, known for his sharply tailored blazers, handlebar moustache and armsleeve tattoos, is more than an arbiter of good taste.

A menswear authority who has spent over 25 years working with leading luxury department stores like Barneys New York, Neiman Marcus and Bergdorf Goodman, as well as directional fashion labels like Thom Browne, Wooster surprised many, last April, when he took up the position of 'Vice president of brand, trend and design' at JCPenney, an ailing chain of mid-range department stores headquartered in Plano, Texas. Importantly, Wooster now works under the company’s new chief executive, Ron Johnson, who boasts a formidable track record as former retail chief at Apple and plans to completely remake the business.

“It’s about upgrading everything,” Wooster tells BoF. “How we think, how we act, the processes that we have in place, breaking down those barriers. It’s taking a very old company and turning it on its ear by treating it as a start-up,” he enthuses. “It’s like the New York Times crossword puzzle. Sometimes you can do it, sometimes you can’t. For me, the ideas are not hard; getting it done is the hard part, because of either existing process or merchants, customers and factories that don’t necessarily see the same thing I do. But I’m not proposing three-armed jackets. I’m just proposing taste at a price.”

Wooster’s love affair with department stores began at a young age, when he was growing up in the small town of Salina, Kansas. “My first exposure to fashion was stores. I’ll never forget the first time my grandfather took me to what is now Macy’s in Wichita, Kansas. My father was a mechanic, so it was a completely different thing for me — a downtown store with escalators! I was just really mesmerised by the whole idea,” he recalls. “As I got into my teens, I realised that if the choice was between mowing yards or dressing up and working at the clothing store, I’m picking the clothing store.”

At 16, Wooster began working at a local family-owned retailer, Joseph P. Roth and Sons, where he had his first brush with buying. “Charlie, one of the sons, took me under his wing. One day, when the salesmen brought their collections to the store, he said, ‘Nicky, come here. Which are the best plaids?’ So I said, ‘That one, that one, that one.’ Then, the tie salesmen would come and he’d be like, ‘Nicky, pick ten ties.’ So I picked ten ties.”

Wooster studied journalism and advertising at the University of Kansas and soon after moved to New York to work for the advertising agency Saatchi & Saatchi. “It was really a terrible fit, because really, being an assistant account executive in those days, you might as well have been an investment banker,” he says. “It was all numbers, tons of spreadsheets and analysing business — and all before computers. But it did give me a fundamental understanding of what drives things and how to drive business. It was really good training in that way. But it was sort of like the army. I didn’t want to do it.”

Indeed, Wooster’s true love was retail and he soon managed to secure a position as an assistant department manager at Saks Fifth Avenue. “It was an amazing time,” he recalls. “Burt Tansky, who went on to become the CEO at Neiman Marcus, was the president; Roger Farah [now president and COO of Ralph Lauren] was the men’s GMM (general merchandise manager); Wayne Meichner [now president of Polo Ralph Lauren Retail] was a men’s sportswear buyer; Linda Beauchamp [who went on to become President and Founder of Donna Karan Men’s] was the men’s fashion director; and Joe Gromek [who became president and CEO at Warnaco] was the store manager.”

But yearning for experience as an assistant buyer, in 1987, Wooster landed at Barneys New York working for Peter Rizzo. “He taught me about fabric, scale, colour, pattern; all the things that I think really lend themselves to any sort of business. Whether it’s high, low, men’s, women’s, kid’s, it doesn’t really matter — the fundamentals are still there.”

Wooster later left buying, becoming director of retail merchandising at Calvin Klein, then design director at Polo Ralph Lauren, then president of John Bartlett. But ultimately, another position caught his eye. “You know, I didn’t even know that such a thing as a fashion director existed until I worked at Saks Fifth Avenue and I realized that there was a person there whose job was not purely about business, but rather about vision. There was a person who got to be the eyes, ears and voice of the store and that appealed to me.”

In his biggest move yet, in 2010, Wooster was named men’s fashion director at Neiman Marcus and Bergdorf Goodman, which is owned by the Neiman Marcus Group. “I was like, ‘Wow.’ I couldn’t believe that I had the good fortune to have that experience,” he says. “I functioned as a filter, a voice, an editor, and a teacher for both the salespeople and the customers.”

But Wooster’s career hasn’t always been smooth sailing. After a year and a half at Neiman Marcus, he was abruptly ousted from his post, reportedly because of a frank interview published in GQ in which he was quoted as having said: “I am just an old f—ing midget queen who, you know, had the good fortune to get this job and it’s like, ‘How did that happen?’”

Soon after, he began advising Thom Browne and Gilt Groupe, where he joined “a dream team of menswear people” including Josh Peskowitz. “We were launching [menswear e-tailer] Park & Bond, which was along the lines of Neiman and Bergdorfs — full-price.” But after less than two years in business, Park & Bond is set to be shuttered following the upcoming holiday season.

Wooster’s takeaway from the experience? “Certain things that work well in physical stores don’t necessarily work well online, because [merchandising online is about making] a great picture. For example, the colour black is something that is really critical to brick-and-mortar retail stores, but it doesn’t translate online. It’s a really tough thing to get that sort of depth, that same richness that you might see in the store.”

In his current role at J.C. Penney, Wooster oversees three intertwined areas: brand, trend and design, travelling frequently between the company’s headquarters in Plano — which he describes as mix between “Mall of America and Narita Airport” — and New York City. “There really isn’t a typical day,” he says. “We do a lot of research and look at what’s happening on the runways, on the street and blogs. And then we communicate those things both internally and externally.” The brand managers “bridge between creative and the merchants. They really look at the business, the history, the performance, as well as the opportunity. And they schedule, coordinate and run the calendar for design, which is the third part of my job.”

Lately, Wooster has been occupied with rethinking the men’s department as a place (not dissimilar to Apple stores) where people want to spend time; “a place for education” and “a place where families want to be, where people want to sit, where there’s technology or toys to keep them occupied.”

An active Tumblr user, Wooster calls the microblogging service his “go-to thing” for inspiration and whips out a camouflage-covered iPhone to prove it. “Tumblr, The Fancy, and Pinterest are all really going to change how we look at things. I’m really interested in how publishing and retail might work together,” he says.

But ultimately, “better taste and offering customers a way to feel better about themselves is, for me, all I really need to focus on,” says Wooster. “I see it in my Twitter feed and my personal Tumblr messages — not only are guys interested in style, they really want to know how they can get it at a good price. That’s really what my mandate is. Everybody likes a deal. Everybody wants to feel that they made the best purchase for their money. If I can offer our customers an upgraded point of view at prices they’re comfortable with, I think it’s a win for everybody.”

So what advice does this self-described “kid from Kansas” turned menswear authority have for aspiring fashion directors? “It’s hard work,” he says. “Get ready to move a lot of clothes! During photo shoots for Gilt, I was the one carrying the clothes, trying to find a taxi in the rain with ten garment bags. And that’s just the tip of the iceberg.”

“It’s so funny,” he adds. “At 28, I really felt like I knew everything. At 52, I can tell you I don’t know anything.”